Halloween in Sleepy Hollow Country

Welcome to this month’s Blogorail Peach Loop. Today we are exploring fun you and your family can have this fall. Lots of fun can be found locally!

Plan a spooky family outing to the home of the Headless Horseman this Halloween season. Updated with 2017 information!

Historic Sleepy Hollow country in Hudson Valley, New York offers a range of activities celebrating Washington Irving’s classic haunted tale.

Sleepy Hollow Country

“In the bosom of one of those spacious coves that indent the eastern shore of the Hudson… there lies a small market-town… known by the name of Tarry Town… Not far from this village, perhaps about two miles, there is a little valley… This sequestered glen has long been known by the name of SLEEPY HOLLOW.”

Follow the Hudson River north from New York City for about 25 miles and you’ll come to the home of Washington Irving, famous for being one of the first American authors. Views of the forest-lined river make this area quite beautiful, especially in the fall.

Irving described this region, writing: “A drowsy, dreamy influence seems to hang over the land, and to pervade the very atmosphere.” It’s a great area to visit, especially around Halloween, since the “the whole neighborhood abounds with local tales, haunted spots, and twighlight superstitions.”

In my opinion, it’s the perfect place to enjoy a warm apple-cinnamon donut and a hot apple cider while listening to a spooky tale on a crisp, October evening.

The Legend of Sleepy Hollow

As a kid, I loved ghost stories. I still do. To me, the “Headless Horseman” is the most iconic of all ghosts when it comes to Halloween. The guy carries a Jack-o-lantern in place of his missing head! He’s the coolest ghost ever!

I think I was about my daughter’s age when I first heard the story of Ichabod Crane and the Headless Horseman. This Halloween will be the perfect time to introduce her to that story. Disney’s classic animated version (narrated by none other than Bing Crosby) can be found online. I think I will also purchase a young reader’s version of The Legend of Sleepy Hollow from Amazon.

Halloween in Hudson Valley

“Sleepy Hollow Country” embraces its history each Halloween with events that celebrate Irving’s classic tale. Some of the events may not be suitable for younger children, but there’s still plenty of reasons to consider making a family day trip or weekend visit.

Each year, over 7,000 pumpkins are hand carved and then arranged to create an experience like no other. Alien landscapes, giant snakes, spider webs, dinosaurs, sea serpents, skeletons… and of course, the Headless Horseman and famous Sleepy Hollow Bridge. This video is from 2013. They keep adding more and more to it each year.

The Great Jack O’Lantern Blaze dates are Sept. 29-30, Oct. 1, 5-9, 12-31, Nov. 2-5, 9-12, 17-18, 24-25. Online tickets are $20 for adults ($25 on Fridays and Saturdays), $16 for children 3-17 ($20 on Fridays and Saturdays), and free for children under 3 and Historic Hudson Valley members.

I strongly suggest purchasing tickets in advance.

The Great Jack O’Lantern Blaze has been the sole reason for our annual Halloween visit to Sleepy Hollow Country so far, but you can explore more of the story with these other experiences.

Horseman’s Hollow

Billed as an “outdoor/indoor ‘period-correct’ haunt”, Horseman’s Hollow is a ticketed event that takes you into the world of a village taken over by the Headless Horseman himself. If you’re looking to be scared, this sounds like it’s for you.

It’s not suitable for young children or for adults who are claustrophobic, or have heart or other health conditions. This is something I would like to experience, but I know that Lisa and the kids would not enjoy it.

Haunted Hay Ride

For one weekend each Halloween, the town of Sleepy Hollow hosts a Haunted Hayride that follows the same path Ichabod Crane is said to have taken the night he was chased by the Headless Horseman. (Irving made up the story, but used real landmarks in his descriptions).

In addition to the hayride, there is a free block party with activities for the whole family. This year, the event is taking place the weekend before Halloween, tickets are not available as of right now.

Irving’s ‘Legend’

Irving’s ‘Legend’ is a faithful retelling of Irving’s classic, The Legend of Sleepy Hollow. The story is told by a live actor in the Old Dutch Church in Sleepy Hollow. The website does not recommend this experience for younger children. I think Lisa and Bella could handle this. It may be a few years before the whole family gives this a try, though.

The Old Dutch Church can be visited during the day for free, without the dramatic story-telling.

2017 info: Irving’s ‘Legend’ dates are Oct. 6-8, 13-15, 20-22, 26-31. Seating is very limited and there are three performances each evening. Online tickets are $25 for adults, $20 for children under 18. Historic Hudson Valley members receive a $5 per ticket discount.

Sunnyside, Home of the ‘Legend’

Visit and explore ‘Sunnyside’, the home of Washington Irving. Sunnyside, Home of the ‘Legend’ includes a tour and family-friendly activities. We’ve yet to visit Sunnyside ourselves, so we’re not sure if the tour still includes a telling of “The Legend of Sleepy Hollow” as it was described as doing in the past. (there is no longer mention of that on the website).

Pairing “Sunnyside, Home of the ‘Legend'” with the Great Jack O’Lantern Blaze is the best option for families with younger children. Leave yourself time in between to get something to eat, but leave room for snacks at the Blaze.

2017 info: Sunnyside: Home of the ‘Legend’ dates are Sept. 30-Oct. 1, Oct. 7-9, 14-15, 21-22, 28-29. Online tickets are $14 for adults, $12 for seniors, $10 for children 3-17, and free for those under 3 and Historic Hudson Valley members.

Headless Halloween Mini Golf

For one day only, play some spooky mini golf at the Warner Library in Tarrytown. This looks like fun if you happen to be in the area on that one day.

Sleepy Hollow Cemetery

The final resting place of Washington Irving offers Halloween events and guided tours both during the day and lantern tours in the evening . While not “scary”, this is not something I would take the kids to right now. Maybe when they are older.

Places to Stay

There are several hotels, inns, and bed & breakfasts in the area. Some of the area hotels run specials for the Halloween events.

Being just 25 miles from New York City, you could also plan your stay around a visit to the Big Apple.

Planning your Visit

We’re fortunate to live close enough to visit each year. We’ve yet to make a full day experience of it yet. Typically, we buy our tickets for the Great Jack O’Lantern Blaze and work out if we’ll have dinner beforehand or afterwards. Perhaps this year we will make more of a day of it, checking out the town of Sleepy Hollow and perhaps stopping by Sunnyside.

We could also work in other fall favorites, like apple or pumpkin picking during the day before seeing the Great Jack O’Lantern Blaze in the evening.

If this sounds like something you’d like to do with your family or friends, check out Historic Hudson Valley’s planning guide. It has some great tips on how much time you’ll need to allot for doing multiple ticketed events on the same day.

Which of these Sleepy Hollow treats most appeals to you and your family? Let us know in the comments below.

For more Fall fun,
check out the other great posts from the Blogorail!

This trip sounds amazing! I’ve watched The Legend of Sleepy Hollow every year since I was a kid and to visit the town of inspiration would be so much fun. I would also love to see The Great Jack-O-Lantern Blaze!

Trackbacks

[…] have been all the rage for the past couple of years. We went to a local one before we discovered The Great Jack-O-Lantern Blaze and we never looked back. We love roaming through display of over 7,000 pumpkins, usually with a […]

[…] Hudson Valley is such a beautiful place. We would love to make a day trip to Warwick, NY for some apple picking or even the apple festival! We love Sleepy Hollow Country in the Fall because of the Great Jack O’lantern Blaze. This year, we are aiming to make it an all-day experience and really immerse ourselves and celebrate Halloween in the place that inspired the Legend of Sleepy Hollow. […]

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